@Louis Jeffries Hi Louis! Thank you for the advice. I never thought about house hacking in the way you said "living where you want to live is priority over creating an investment opportunity." This is very true and I will have to consider what I am willing to sacrifice. I have looked at the 203k loan, but I am not sure why I did not go about that in more detail as a potential option. Also, I may be wrong, but I believe in order to obtain a 3-4 unit building I need somewhere around 2 months+ of reserves which, in this case, I do not have enough for in the areas I was looking at considering down payment, financing costs, etc.
@Allen L.
Thank you Allen! Did you invest in Chicago specifically or are you based out of San Fran. entirely? I will definitely take your recommendation and look into the 203k loan. I currently have financing in place, so I definitely will ask for the loan to be adjusted to conform to 203k standards compared to the normal FHA loan. I will be in touch once if I find anything out!